My chess credentials are not strong, but the fact remains that I did once play the grandmaster Garry Kasparov. I was a member of a team at a charity event during which Kasparov gave a simultaneous exhibition, playing 20 games of chess at the same time. He prowled from table to table, barely pausing to look at each board before making abrupt moves that somehow dispatched all his opponents.

For me, the event was memorable because of the look of puzzlement on Kasparov’s face when he returned to our table and found that we were still continuing to push our diminishing number of pieces doggedly around the board, like a chess-playing version of the Black Knight in Monty Python and the Holy Grail. Anyone with any real knowledge of the game would have resigned after our first 10 moves.

Clearly the gulf between me – with no grasp of opening theory and no natural aptitude for the game – and Kasparov is immeasurably vast. And yet, he and I were able to play together, however briefly. As Stephen Moss points out in The Rookie, it would be hazardous for any amateur to venture into the boxing ring with heavyweight champion Anthony Joshua. I wouldn’t risk my health on a cricket pitch against a fast bowler and my forehand is unlikely to trouble Serena Williams. Yet chess’s cerebral nature lured me into the belief that my team, Deep Purple, might have an outside chance of a battling draw. They’re the same 64 squares, for everyone, after all. Or are they?

Moss, a Guardian journalist, ponders questions like these as he sets out on a chatty, funny and strangely absorbing journey through the world of chess. He meditates on the nature of mastery and commitment, success and failure, and the meaning and the purpose of the game. And he chastises himself – a lot – for shortcomings both existential and chess-related.

Other middle-aged men might buy an inappropriate sports car. Moss resolves to get better at chess

Early on, he diagnoses his personal failings with a certain harshness, berating himself for his lack of focus and commitment. Having crossed the halfway point of his life with nothing substantial to show for it, he decides his salvation lies on the chessboard. Other middle aged men in his position might sign up for a triathlon or buy an inappropriate sports car. Moss resolves to get better at chess. The loose structure of the book follows his two-year struggle to raise his lowly chess grade – 133 at the outset – and achieve some kind of mastery of the game.

Moss divides his book into 64 sections that correspond to the chessboard squares. They track his progress through the rankings, as he competes at chess tournaments in the UK and gatherings in the Netherlands, Russia, Gibraltar and the US. Along the way, he encounters notable figures from the world of chess and reflects on the history and broader cultural significance of the game. The Rookie is also an erudite survey of the literature chess has spawned, much of which perpetuates the notion of the chess-player as an obsessive misfit.

A chessboard may be black and white, but the palette of Moss’s book is shades of grey. There are cash-strapped chess tournaments in tatty seaside towns, many redolent of male body odour, and an overall sense of a once-great game in a kind of terminal retreat. Throughout, Moss is dogged by a feeling that he’s writing an elegy for the game. At one time, the chessboard was a proxy battlefield for the cold war; as recently as 1993, Channel 4 broadcast live coverage of Nigel Short versus Kasparov. Today, gifted grandmasters are struggling to get by on a pittance. Moss even wonders if there’s any point in chess now that computers are better at it than humans.

So the reader is grateful for his excursions to Moscow and the energy of the chess hustlers in Greenwich Village. It’s uplifting to encounter a handful of enthusiastic female players, and colourful figures such as Vladislav Tkachiev, the self-described Pete Doherty of chess, who claims to think about the game while making love to his girlfriend. In St Louis, Missouri, at least, the game has been re-energised by the money of the billionaire chess fanatic Rex Sinquefield. And the reader is relieved, above all, for Moss’s own slow and hard-won progress as a player.

He’s an amusing, self-deprecating guide. Despite the best intentions, he can’t stay off the beer or sausage rolls or bring himself to open the books on chess strategy that he knows he ought to be reading. He gets drunk, falls into the sea, hums while he plays and fails to keep up the pretence of good sportsmanship after yet another crushing defeat by a child or retired accountant.

Written for a general audience, relative experts would get pleasure out of it – not least that of schadenfreude

The Rookie is written for a general audience, but I imagine relative experts would get pleasure out of it – not least that of schadenfreude. An appendix includes 10 of Moss’s games in algebraic notation, with commentary by the former international chess player, John Saunders. Sample observation: “a desperately dull opening, for which I would normally give Stephen my slightly more middle-class version of the Alex Ferguson hairdryer treatment, but since he only needed a draw, it was forgivable just this once.”

Yet despite Moss’s assertions to the contrary, he does have a kind of desperate doggedness, eating up drubbing after drubbing in benighted clubs like a chess-playing Rocky Balboa. “Live like a man, fight like a dog,” one pugnacious grandmaster advises him, though it’s perhaps hard to imagine Rocky being reminded by his cornerman that “everything depended on me: I had the fate of Kingston second team on my hands.”

It’s not a plot spoiler to reveal that Moss is still some way from chess stardom, but his book succeeds admirably as a celebration of the game. It certainly reminded me of the satisfaction that chess gives and the astonishing way it conjures infinity out of its 64 squares. By the end, The Rookie will have readers dusting off old boards in order to investigate the delights of the Nimzo-Indian, the Ruy Lopez or Sicilian Poisoned Pawn, and dreaming of glorious showdowns with a grandmaster.

•The Rookie is published by Bloomsbury. To order a copy for £15.57 (RRP £18.99) go to bookshop.theguardian.com or call 0330 333 6846. Free UK p&p over £10, online orders only. Phone orders min p&p of £1.99.